X0306 4 2020-08-11 0 0001433714 CASTLIGHT HEALTH, INC. CSLT 0001742487 O'Meara Maeve C/O CASTLIGHT HEALTH, INC. 150 SPEAR STREET, SUITE 400 SAN FRANCISCO CA 94105 1 1 0 0 Chief Executive Officer Restricted Stock Units (RSU) 2020-08-11 4 A 0 344828 0.00 A 2021-08-16 Class B Common Stock 344828 689656 D Each restricted stock unit ("RSU") represents a contingent right to receive one (1) share of the Class B Common Stock upon settlement for no consideration. The first installment of shares underlying the RSUs was earned on November 16, 2019 and reported on a Form 4 filed with the Securities and Exchange Commission on November 19, 2019. The second and final installment of shares underlying the RSUs was earned on August 11, 2020 and are being reported on this Form 4. All shares underlying the RSU vest on August 17, 2020, subject to the continued service of the Reporting Person on such date. /s/ Alex Shvartsman, by power of attorney 2020-08-12